{"title":"Palladium-Catalyzed Cross-Coupling Reactions of Carboranes with Alkenes via Selective B–H Bond Activation","authors":"Jia-Rui Chang, Hou-Ji Cao, Yan-Na Ma, Xuenian Chen","doi":"10.1021/acs.orglett.5c00059","DOIUrl":null,"url":null,"abstract":"A palladium-catalyzed Heck-type cross-coupling reaction of carboranes with alkenes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was realized. This reaction shows good B(9) selectivity for <i>m</i>-carboranes and is also suitable for <i>o</i>- and <i>p</i>-carborane. Meanwhile, a series of mono-, di-, and trisubstituted alkenes were compatible substrates to afford the alkenylated products in 16–89% yields. The 1,2-bis(carboranyl)ethylene was first synthesized by the reaction of vinyltrimethylsilane and <i>m</i>-carborane. Further transformations of the C═C bond in the product were examined by hydroboration oxidation, oxidation, hydroboration, and bromination reaction to generate corresponding B(9)-functionalized <i>m</i>-carboranes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00059","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A palladium-catalyzed Heck-type cross-coupling reaction of carboranes with alkenes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was realized. This reaction shows good B(9) selectivity for m-carboranes and is also suitable for o- and p-carborane. Meanwhile, a series of mono-, di-, and trisubstituted alkenes were compatible substrates to afford the alkenylated products in 16–89% yields. The 1,2-bis(carboranyl)ethylene was first synthesized by the reaction of vinyltrimethylsilane and m-carborane. Further transformations of the C═C bond in the product were examined by hydroboration oxidation, oxidation, hydroboration, and bromination reaction to generate corresponding B(9)-functionalized m-carboranes.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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